DISCLAIMER:
The following story is entirely fictional, and contains depictions of 18 year olds in sexual situations with minor teenagers no more than forty-eight months younger than those of legal age. All parties depicted herein are behaving consensually and entirely inside the jurisdiction of either the U.S. State of Maine or New Jersey where such relationships are legal. This work is in no way meant to endorse or depict illegal sex of adults with minor children, or forcible sex with unwilling participants, and shall not be construed as such. Sexual relations between participants of such disparate ages is prohibited by law in much of the world, including most of the United States, and in some jurisdictions possession or viewing of such material may be banned. Readers are entirely responsible for knowing and obeying the laws in their area. The author assumes no responsibility or liability for criminal or other charges placed upon individual readers in such jurisdictions for any reason. By reading beyond this disclaimer you assert that... 1) You are over the age of 18 years old, or over the age of 13 with the permission of a parent or legal guardian (Individuals under the age of 13 are strictly prohibited from reading this story) 2) You have read and understood the contents of this disclaimer, and waive all legal recourse against the author for such liabilities including, but not limited to, those described herein.
All Rights Reserved.
The House Boy's Summer Chapter 1: Nerves Part 4: The Game -----------------------------------------------------------------------------
"The game we're going to play," Chris said, lying down and putting his sunglasses back on, "will test your physical stamina as a gay guy. I'll instruct you to assume three sexual positions, and you'll try to hold them without dropping the dildo. You start off the game with 0 points, each time you hold both the position and the dildo you get a point, and each time you drop the dildo or the position you lose a point." Chris crossed his hands on his chest and looked at me like I was about to be had, "When you drop the dildo, it will be re-lubricated and reinserted, making it harder to hold on to. If you end the game with negative points you're punished, but if you earn three points you get to cum in a fourth position of your choice."
My heart was pounding again and I felt myself wishing for another beer, but instead all I said was, "Yes sir, what will be my first position?"
"We'll make the first position easy: doggie style. Get up on the chair on your hands and knees." I instantly climbed onto my chair, with my boner pointing achingly downward. I could feel that the sun on my back would grow hot soon, and wondered idly how long I'd have to hold each position.
Almost as if he knew the question I was asking, Chris placed an open beer down on my chair beneath me, "Just to make this position minimally difficult, knocking this beer over means you lose, agreed?"
"Agreed," I said, adjusting the dildo, which had slipped out a little as I got onto the chair.
"We'll change positions when you finish the beer, and you can only lift the can with your right hand," Chris sipped from his beer and laid his head back, "And go." At first I wasn't really sure what to do. Kneeling down on my hands and knees with a dildo in my ass was definitely satisfying; I could imagine cumming just from closing my eyes and rocking my body back and forth. However, I did this at the risk of knocking over the beer, so I decided that the best course of action was to play the game, picking up my beer and sipping slowly at the can.
Chris smiled as he looked at me, "Pretty easy position, right?"
I thought about the dildo, which wasn't slipping out of my ass in any important way, and then about the cold beer in my hand, "Drinking this beer might give me neck strain," I suggested with a laugh, "but other than that it just feels good."
"Well don't cum or anything," Chris pointed at my hard dick and nodded like it proved his point, "cumming while playing is worse than losing with negative points."
I gulped down more of my beer, "What happens if I have to piss while playing?"
"You hold it," Chris said, but then stopped himself with a smile, "though I don't envy you if you have to go real bad, because you'll almost definitely drop the dildo."
I continued to drink my beer, and wondered if its point was to cause me this aforementioned difficulty: maybe he was trying to ensure that I didn't get to three points. Once I got about half way through the can, however, I decided that the best solution to the problem was to just drink the beer as fast as possible. Chris just watched with a puzzled expression as I downed my beer, and as the last drops went down my throat he reached over and gave my cock a hard flick, causing me to grunt softly. "Decided to finish the easy one fast?" He said playfully, "No problem. The next position is fast too. Stand up, I'm taking you over to the grass."
I started to move backwards across the chair but could feel the butt plug slipping slowly out of my ass as I shimmied, so I placed my left hand over the base of the instrument and held it in place as I pushed myself up onto my knees. My boner popped happily out in front of me, and I could feel its heat as it basked in the sunlight. I looked proudly over at Chris, with my hand on my rounded ass crack and abdominal muscles on display, I felt like quite an enticing site to behold. He seemed to approve and gave me an encouraging smile, even giving my dick a squeeze as he stood up and grabbed the lube. "Let's go," he commanded, and I followed suit eagerly while the butt plug ground deeply into me like an internal extension of my rock hard dick.
"These next two positions," Chris began as I waddled behind him and over to the grass, "are a lot more difficult than that first one, but you'll notice all of them are useful in preparing you for sex." I tried to focus on Chris's words, but was having difficulty with the muscular globes of his naked ass moving in full view. He didn't seem to notice, however, and just continued talking, "This next position is an action position, since you can't really drop the dildo in any real respect. You're going to stand on your head and present me your ass, and I'm gonna pull the dildo out and then drop it back into you."
I must have been kind of drunk by then, because his words didn't really have the effect on me that they should have. When he pointed at the grass and said, "Do a headstand," I clearly had no logical idea of what I was getting myself into. I had an alcohol and sex induced smile on my face as I got down on my hands and knees and placed my forehead against the ground. As I pushed myself onto my head, trying to hold the dildo in place by clenching my ass muscles, I looked at the upside down feet of Chris with amusement.
"Balance your legs on your elbows," he instructed, walking behind me and out of view, "give me a good view of your ass." I complied, resting my legs down in a more comfortable position. The dildo was sticking slightly out of my ass, but as soon as I had rested my knees against my elbows it started to slide slowly back into me. "I should probably warn you," he said, putting his hands on my ass, "you're going to fail this position." With that he pulled on the base of the dildo, and I could feel its long slender form slide as it made its way out of me. Chris pulled it up until it was about half way out, then stopped and simply let go of it entirely. Since I was standing on my head with my ass pointed almost directly upwards, the butt plug began sliding slowly into my ass strictly due to gravity; the main resistance it experienced was my sphincter, which began pulsating from the abuse. I tried to take deep breaths in order to relax my stretching muscle, and with each breath I took the butt plug slid further and further into me.
"Good job," Chris commented as the plug finished its slide into home, "How does it feel?"
He pulled the plug back out of my ass and released it again, still balanced inside of me. As it started its slide back downward the friction became worse than before and I had no choice but to grunt softly at the heat on my muscles, "There's not enough lube," I replied to Chris's question, "My asshole is kind of burning and I feel like I'm taking a reverse shit."
Chris laughed, "Yeah, part of the problem of upside down positions is that the lube slides into you more easily then the dildo. It'll probably come rushing out as soon as you get back right side up."
I didn't really like the sound of this, but couldn't concentrate on my thoughts about it. Instead, my mind was almost totally focused on the drying plug which fell heavily into my body, causing me to wobble a bit on my head, "This position is hard," I declared drunkenly, "could we do a different one?"
Chris pulled the dildo back out of me, much to my dismay. The apparatus was almost completely dry now, and the friction was pure torture. I half hoped that he would pull it entirely out of me and agree to try something else, but he didn't. Instead he just let go of it again, and let it continue on its burning slide passed my sphincter and into my ass. The sensation was mind boggling as it slid down and into me for a third time. The dry sides of the toy were wrecking havoc on the walls of my hole, and I could feel the burning sensation bringing tears to my eyes. My dick, which moments before had been pointing eagerly out over my head and towards the pool, was losing some of its hardness. Unfortunately I couldn't stop it from being semi-hard since the dildo kept encouraging my insides to keep it erect.
"Chris," I implored, "Master Chris, it really hurts."
Chris didn't seem sympathetic, "If it hurts then break the position and we'll do another one, but it'll mean losing a point." The dildo had made its way back inside of me, and Chris didn't waste any time in pulling it back out. My sphincter was on fire now, and I could see that Chris was right about me not passing this position. As the long tool made its slow descent back into my ass for the fourth time sweat and tears were mingling unhappily on my face. My deep breaths were no match for the amount of abuse my tight hole was taking, and it was all I could do to keep from crying out.
"Please," I begged Chris, "Stop. Just let me rest for a second."
"Rest?" Chris grabbed hold of the dildo and stopped its incessant slide, much to my relief. I let out a grateful sigh, and had almost uttered the words "thank you" before Chris began manually fucking me with the drying toy. It was a slow up and down, but enough to make the volume of tears on my face increase.
"Agh!" I cried, not sure what else to do, "it burns so badly."
"Want it to stop?" Chris taunted with a bit of a joke in his voice, "want the big bad dildo to stop fucking you?"
"Yes!" I replied on behalf of my aching anus, which felt like it was seconds away from being torn apart, "Yes! Please stop!"
"Only if you agree you've lost this position," Chris replied, continuing to bring the dildo up and push it back in at a steady pace.
"I've lost the position!" I agreed, "Now please stop." Thankfully Chris didn't seem to have much of a sadistic streak in him, and he stopped the abuse on my hole after driving the dildo home one last time. He instructed me to stand up, but to maintain my grip on the dildo, which was an unsurprisingly difficult task after the abuse my muscles had just taken. As I stood up, my legs were shaking, and I had to visibly wipe the remaining tears from my eyes, "That was not fun." I told Chris, wondering if that was his intention from the start.
He nodded, "It's not fun now, but once you get the hang of it that position won't be so bad." He began back towards the chairs and motioned for me to follow, "To tell you the truth though, I expected you to last longer in that position than you did. I would've let you win after ten gravity drops, but you were being kind of a baby about it."
"A baby?" I looked down at my shaky legs and wondered if any guy could've easily withstood what Chris was suggesting, "I'm sorry sir."
Chris smiled and shrugged, "Not as sorry as you're going to be, I don't think you'll be able to handle this next position either, if you couldn't handle that one." We arrived back at the deck chairs and Chris sat back down on his, signaling for me to stay put. "This next position that you're going to do," Chris began, "is called the squat. Basically you're going to spread your legs, bend your knees and point your ass towards the ground." Chris reached down into the cooler and grabbed a couple more beers, "How drunk are you?" He asked me.
I thought about it for a moment and then decided that I was "drunk, but not sure how drunk," which Chris seemed to take as an indication that I could handle another beer. Popping open the top of one, he handed it to me and instructed, "To make this easier on you, we'll say that you're done with this position once you finish the beer." I nodded compliantly, still taking deep breaths in order to relax my body. I assumed a squatting position, and was instantly thankful for my strong and capable leg muscles which were holding my ass above the ground. As soon as my hole was pointed I felt a rush of fluid, and the dildo suddenly seemed to be as well lubricated as it ever had been. It instantly started to fall out of my ass and towards the ground, and I had to use my left hand to keep it inside me. "Ready?" Chris asked, and I nodded, "Go," he commanded.
I lifted my left hand off the base of the dildo and began clenching desperately at it with my ass muscles while trying to take large deliberate gulps from my beer. My ass, however, was in no shape to be gripping so tightly, especially to something that was suddenly so well lubricated. As I drank, I could feel the dildo slipping slowly but surely out and towards the ground, and found myself wishing that I could hold it into place with my hand. "Wow," Chris commented as he watched me in my struggle, "it's oddly satisfying to watch that thing slide out of you."
"Uhhh," Was my unintelligent reply, "how far out is it?"
"About a third of the way," Chris smiled, stretching his hands over his head, "How far along are you with your beer?"
I shook the fluid inside the can, only to find that I wasn't making very much progress. The need to pee was quickly resurfacing as I tried to force the drink down my throat, and I was finding it difficult to continue. To make matters worse, as I was considering Chris's question I temporarily lost my grip on the artificial staff, and it slipped almost entirely out of me. I whimpered a bit as I tried to regain control of the object, but Chris seemed only amused. "You're almost done there, that thing is hanging over half way out of you." As if agreeing with Chris's assessment, my leg muscles picked that exact moment to start acting up, and they began to shake again, I tried to force more of the beer into me, but I still had nearly half a can to go and was positive I couldn't finish before the dildo slipped completely out of me.
Regardless of my pessimism I made a distinct effort to finish the position. I clenched my sphincter around the dildo as tightly as I could, though I wasn't sure that it was really helping me hang on to the object. I kept taking gulps of the beer, as big as I could manage, but my ability to chug it had been significantly compromised by the way my stomach muscles had to clench in order to compliment the effort of my backside. I looked over at Chris for encouragement, thinking that I was doing well not having dropped the position yet, but he seemed to be focused on the dildo sliding out of my ass. In response to my look he simply took another sip of his beer and said "only one third left to go," as if I had been asking how close I was to failing.
Unfortunately, this was not the encouragement that I was looking for, and as I nervously drank gulps of my beer I could feel the dildo sliding out of me little by little. As the staff slowly made its way out of me I could feel a slight burning sensation on my insides, one which my legs were matching in force. By the time the head of the apparatus had reached my tightly clenched opening I only had three or four gulps of beer left, and while my confidence had gained I still wasn't sure which one of us would win the race. Fortunately, the head was slightly larger than the rest of the staff, and its ridges rested more easily against my enclosed muscles. I gulped desperately at my beer, trying to prove to Chris and myself that I wasn't a complete failure at this game.
Chris seemed pleased, "Hey, you're really hanging on to the head there for dear life aren't you?" He taunted, but with my beer tilted up above my head I couldn't really see his face. My leg muscles were on fire now, and my ass felt the same way. My body was practically begging me to give up, but my mind was focused on finishing the beer. As I gulped down the last few drops of the can I could feel my ass muscles giving way. Not wanting Chris to think that I cheated, I raised the empty can triumphantly over my head, its fluid still in my mouth. I crushed the can in my hand to show that it was empty, thankfully letting my sphincter give way and the intruder fall to the ground.
Chris whooped proudly, "Good going man," He congratulated me as he clapped a bit, a huge smile on his face, "I really didn't think you could do it at the end there."
"Thanks," I responded, bringing my wobbly legs back up into a standing position. My dick had lost most of its hardness by this point and my body was covered in sweat. My ass felt like a fist had been through it, and any attempts to clench my cheeks together were met with even shakier legs. I frowned unhappily at Chris, "That game was really difficult," I said, "I'm exhausted."
Chris sighed and put his hands behind his head, looking at me like I was some sort of prize, "Well, that game gets better with practice."
I looked at Chris for a moment, standing there awkwardly awaiting instructions. He didn't say anything, however, so I decided to assume the inspection position. Chris smiled happily at this, "You're cute, you know that?"
"Thanks sir," I replied, "is there anything you'd like me to do for you?"
Chris laughed, "Don't tell me you're still horny. I thought for sure that game would fuck it out of you."
I nodded, "It did sir, but I think I'm too tired to keep standing here."
"Oh!" Chris pointed at the chair, "I didn't realize you were waiting for permission, you can totally lie down, you deserve a break."
I dropped my arms and plopped myself face first onto the chair, used ass to the sun, "Thanks," I sighed, closing my eyes, "that game was really hard."
"Yeah," Chris mused, "you said that already."
"Sorry," I replied, "I'm drunk." ----------------------------------------------------------------------------- Author's Notes:
So that's the end of Chapter 1. I was hoping to get this part out more quickly since it went pretty readily with part 3, but oh well. Chapter 2 will probably be a bit more dialogue heavy, so I hope you'll all stick with me as I work through what's happening in a bit more detail. I'd like to extend a continuing thanks to everyone that's given me feedback. If any of my readers have stories of their own let me know, I'd love to look at what you guys are writing. That, or any other thoughts, comments, questions, and general hellos can be sent to RyanHartBooks@Yahoo.com, and I'll do my best to get back to you as quickly as I can.
As always, thank you to Alex Kerr from fanfiction.net. Without your edits this story wouldn't be where it is today.